This invention relates to reactions of fluoroalkenes with fullerenes, and the cyclofluoralkylated products derived from these reactions.
Recent success in synthesizing macroscopic quantities of carbon clusters such as C.sub.60 and C.sub.70 (known as fullerenes), by W. Kratschmer et al., Nature, 347-354 (1990), has opened the door to the study of this new class of organic compounds. Kratschmer et al. describe the fullerene molecule C.sub.60 (also known as buckminsterfullerene) as a centrosymmetric truncated icosahedron. Pure solid buckminsterfullerene consists of somewhat disordered face centered cubic or hexagonal close packing of the centrosymmetric molecules. Isolation and characterization of higher fullerenes, specifically C.sub.76, C.sub.84, C.sub.90, and C.sub.94, have been disclosed by Francois Diederich et al., Science, Vol. 252, pages 548-551 (1991). Mixtures of giant fullerene molecules, e.g., C.sub.540, have been discussed by C. Smart et al., Chem. Phys. Lett., Vol. 188, No. 3,4, pages 171-176 (Jan. 10, 1992).
Fluorinated alkenes are known to undergo thermal cycloaddition with themselves and other alkenes to form fluorocyclobutane rings (Hudlicky, M., "Chemistry of Organic Fluorine Compounds, 2nd ed.", Ellis Horwood Ltd., pp. 450-463, 1976). Buckminsterfullerene (C.sub.60) has been proposed to undergo photochemical cycloaddition with itself in the solid state (Rao, A. M.; Zhou, Ping; Wang, Kai An; Hager, G. T.; Holden, J. M.; Wang, Ying; Lee, W. T.; Bi, Xian Xin; Eklund, P. C.; et al., Science, 1993, vol. 259. pp 955-7). Benzyne (generated as an intermediate in situ) is reported to add to C.sub.60 (Tsuda, M.; Ishida, T.; Nogami, T.; Kurono, S.; Ohashi, M., Chem. Lett., 1992, No. 12, pp 2333-2334; Hoke, II, S. H.; Molstad, J.; Dilettato, D.; Jay, M. J.; Carlson, D.; Kahr, B.; Cooks, R. G., J. Org. Chem., 1992, vol. 57, pp 5069-5071). Quadricyclane is reported to thermally add to C.sub.60 (Prato, M., et al., J. Org. Chem., 1993, vol. 58, pp 3613-3615). There are no known examples of the thermal 2+2 cycloaddition of an alkene to C.sub.60 or other fullerene in the literature. Earlier filed, commonly assigned U.S. Ser. No. 08/021,395, now U.S. Pat. No. 0.5,354,926, discloses fluoroalkylated fullerene compounds.
An object of this invention is to provide a mixture comprising cyclofluoroalkylated fullerene compounds by reaction of fullerenes with fluoroalkenes.